I made one monogram-like logo awhile ago:
Here's what I came up with:
All of it was created in Illustrator. I typically find Photoshop easier to use, but I wanted the logo to be in an entirely vector format. The monogram was drawn directly in Illustrator and probably took the most time. I really wanted to add a cameo or poop bags or poop scoopers to fuse classy and tacky and underscore the playfulness and lowbrow nature of Coat and Tails, but it was too distracting. Perhaps in a future iteration. (There's my noncommittal nature coming through.)
Obviously, I want the logo to reflect a Victorian aesthetic, but I also don't want the lettering to be too complex and ornate, since that can impede clear printing and readability. So I decided to base the font for "Coat and Tails" on Garamond Bold. Garamond has a classic, old-world feel, but it's also readable. To allude more directly to a Victorian aesthetic, I added Westerny serifs to the top, middle, and bottom. Also, to achieve symmetry, I adjusted the kerning so that "Coat" was as wide as "Tails".
The "Pet Portraits" font is based on Engravers MT Bold. This is a less readable font than Garamond, but it's less important information, so I allowed it. Here's the original font:
Engravers MT Bold
Here's how I changed it:
Modified Engravers MT Bold
I wanted to add another layer of complexity to match "Coat and Tails", so I added a shadow with its own bottom serif:
Final Modified Engravers MT Bold Font
So there's your glimpse into how the logo happened. I basically spent one day on it because that's pretty much all the time I had.
Now it's back to drawing.